Transformative Leadership Conversations with Winnie da Silva

Winnie da Silva
Transformative Leadership Conversations with Winnie da Silva

Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

  1. Leading with a Global Lens with Anna Gudmundson

    2D AGO

    Leading with a Global Lens with Anna Gudmundson

    “There is a knowing in me that beneath that cultural layer, we’re the same. It sounds so obvious, but it has made me show up in different ways.”  - Anna Gudmundson What does it really take to lead with purpose when you’re building a life - and a business - in a country that’s not your own? In this episode, I sit down with Anna Gudmundson, CEO of Sensate and a global tech entrepreneur whose story spans six countries and countless transformative lessons. We explore what it means to lead as an immigrant, how to build a business without losing yourself, and why cultivating nervous system resilience might be the most overlooked leadership strategy today. Anna’s clarity, humility, and global lens make this conversation both grounding and expansive. You'll hear us discuss: How Anna's early childhood in rural Africa shaped her core belief that "beneath that cultural layer, we're the same"Her journey from Sweden to France, Spain, London, and eventually Los Angeles - and how each culture revealed something new about leadership and herselfWhat it means to create a startup culture rooted in presence, intention, and human connection, not just productivityWhy self-awareness and adaptability are non-negotiables for leading diverse, high-performing teamsThe emotional cost of immigration and how Anna deliberately builds belonging in new environmentsHow Sensate helps people calm their nervous systems through infrasonic sound - and why Anna believes calming the body is foundational to leadershipThe challenge of building company culture while fundraising, and how she uses values to guide everyday decisionsA refreshing take on feedback, safety, and why we don’t need to be liked to be effective leaders Resources Anna Gudmundson on Sensate | Sensate Instagram | LinkedIn Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    58 min
  2. Immigrants Built This with Winnie da Silva

    JUL 9

    Immigrants Built This with Winnie da Silva

    “Immigrant entrepreneurs navigate challenges, build thriving businesses, and show us what leadership can look like when resilience and reinvention go hand in hand.” What if the real secret to America's success isn't who was born here, but who chose to come here? In this episode of Transformative Leadership Conversations, I discuss the powerful and often overlooked role immigrant entrepreneurs play in shaping not just our economy but our national identity. As we celebrate America’s 249th birthday, I reflect on our roots as a nation of risk-takers and builders, and why the immigrant experience may just hold the most valuable leadership lessons of all. You’ll hear stories from my own family, eye-opening statistics, and a rich preview of three extraordinary women leaders joining the podcast this month. You'll hear me discuss: Why America’s business roots run deeper than the Mayflower and how commerce, not just freedom, shaped our beginningsHow immigrant entrepreneurs today are driving business innovation and economic growthWhat history gets wrong (or leaves out) about our “founders” and how that continues to shape opportunityThe four essential leadership traits every entrepreneur must master and why immigrants might be uniquely equipped to embody themPowerful personal stories from my husband’s family and their multigenerational legacy of business-building in the U.S.How resilience, adaptability, a growth mindset, and comfort with risk are more than buzzwords - they’re survival skillsWhat you can expect from upcoming conversations with three phenomenal immigrant women leaders Resources Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    19 min
  3. Coaching Teens into Leadership with Lorraine Connell

    JUN 25

    Coaching Teens into Leadership with Lorraine Connell

    “Leadership isn’t about being perfect or popular. It’s about making decisions, taking responsibility, and developing the skills that allow us to show up with courage and confidence.” - Lorraine Connell Are we unknowingly holding kids back by tying leadership to titles, popularity, and perfection? Could our entire approach to teaching leadership be setting young people up to fail before they even begin? In this episode, I sit down with Lorraine Connell, former chemistry teacher turned teen leadership coach and founder of Peers Not Fears. Lorraine shares how her own experience of feeling “average” in school shaped her deep commitment to redefining leadership for young people. Together, we explore what happens when we empower teens before they’re handed official titles and how we can help them develop confidence, decision-making, and real leadership skills - long before they enter the workforce. You’ll hear us discuss: How our myths around leadership - like needing a title or being perfect - hold kids (and adults) backWhy Lorraine believes the only true requirement for leadership is the ability to make a decisionThe damage caused when we make student leaders into role models who aren’t allowed to failHow mistakes (including Lorraine’s own) became the turning point for creating Peers Not FearsThe power of peer mentoring and why it’s more impactful than top-down leadershipWhy confidence and leadership are inseparable - and how labeling kids can stall bothWhat leadership development actually looks like between ages 12 and 16How games, group coaching, and creative challenges open teens up to growthWhat adults need to remember about owning mistakes and modeling leadershipHow to reframe leadership not as a ladder—but as something wide enough for everyone Resources Lorraine Connell on Peers not Fears | ''Leadership for Our Kids!'' Facebook Group | Lorraine's books on Teenage Leadership I LinkedIn Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    48 min
  4. Teens Take on Leadership

    JUN 18

    Teens Take on Leadership

    "All leaders should be leading with kindness and empathy and respect for other people, which in general, I think means by leading with example." - Aradhna da Silva  Could the clearest vision for future leadership come not from boardrooms, but from high school classrooms? In this episode, I flip the mic and turn to the next generation. After speaking at my daughter’s high school career day, I invited students to share their raw, unfiltered thoughts on leadership - what it is, what it isn’t, and what they would change in the world if they were in charge. Their answers surprised me, inspired me, and reminded me just how powerful honest conversation can be. You will hear: How today’s teens define great leadership through traits like empathy, kindness, and flexibilityWhy many young people believe being feared or cold isn’t necessary - or even effective - as a leaderHow the myth of “born leaders” is being firmly rejected by this generationWhat gives Gen Z hope, and why justice, equality, and inclusion top their list of prioritiesHow students would lead change today - from political reform to creating unity in divided communitiesReflections on how media, culture, and current events are shaping young people’s ideas of power and corruptionA heartfelt wrap-up conversation with my daughter Aradhana da Silva on what her generation truly expects from leaders Resources Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    20 min
  5. Next-Gen Views on Leadership with Winnie da Silva

    JUN 11

    Next-Gen Views on Leadership with Winnie da Silva

    “If we’re serious about developing the next generation of leaders, we have to be just as serious about questioning the models we’re handing down.”- Winnie da Silva Is Gen Z quietly rewriting the rules of leadership - and are we even paying attention? Seventy-two percent (72%) of Gen Z would prefer a non-managerial path to career advancement. They see leadership roles as too high stress and low reward. In this episode of Transformative Leadership Conversations, I talk about how our next generation of leaders - specifically Gen Z - is reshaping what leadership looks like from the ground up. From their desire for trust and transparency to their rejection of traditional management roles, Gen Z is showing us a very different vision of what it means to lead and be led. Maybe it's time we listened a little more closely. You'll hear me discuss: What shaped Gen Z’s leadership perspective, including a timeline of major global events that defined their coming of ageHow growing up in constant instability impacts what they want from leaders at workKey findings from three major studies on Gen Z and leadership, and what those results reveal about trust, vulnerability, and empowermentWhy Gen Z is stepping away from middle management, and what “conscious unbossing” actually meansHow companies say they value people leadership but often fail to show it through actions, compensation, or trainingWhat the IKEA peg analogy reveals about the invisible, underestimated work of leading peopleTwo practical shifts we can make to better support emerging leaders today and redefine what leadership growth looks like Resources Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    15 min
  6. MAY 28

    Listening as a Leadership Strategy with James Misner

    "I think we overestimate the importance of knowing and underestimate the power of listening." - James Misner What if the biggest thing holding back real change is the way we try to create it? In this conversation of Transformative Leadership Conversations, I speak with James Misner — a leader, storyteller, and deep thinker who challenges how we show up for others, especially those on the margins. His perspective is both disarming and inspiring. James pushes us to rethink our assumptions about helping, belonging, and transformation — and why presence might just be more powerful than any plan. This episode is a call to slow down, to stay curious, and to build something deeper than solutions: real human connection. You’ll hear us discuss: Why belonging isn’t just a warm feeling but a foundational need that must come before trust, belief, or any lasting change.How systems that focus on outcomes instead of relationships can unintentionally harm the very people they are meant to support.The importance of being willing to walk with someone through their pain and uncertainty, rather than trying to rescue them with quick fixes.What can shift when we stop treating people as problems to solve and start seeing them as neighbors with stories, strengths, and dignity.James’s personal journey of letting go of the pressure to always have the right answer and choosing instead to offer presence and patience.How discomfort and tension can be invitations to stay and engage more deeply, rather than reasons to step back.The quiet but radical impact of showing up consistently, without an agenda, simply to let someone know they’re not alone. Resources James Misner on The Kipos Group | LinkedIn Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    39 min
  7. Power, Dignity, and Crisis Leadership with Rebecca Vander Meulen

    MAY 21

    Power, Dignity, and Crisis Leadership with Rebecca Vander Meulen

    ‘’Even in a non-profit context, issues of sharing power and mutual respect and dignity are essential and not universal.” - Rebecca Vander Meulen What does it take to lead with courage, clarity, and compassion when the systems around you collapse—almost overnight? In this episode of Transformative Leadership Conversations, I speak with Rebecca Vander Meulen, Executive Director of the J.C. Flowers Foundation. Rebecca has spent over two decades working in global health, faith-based development, and cross-sector collaboration—from launching HIV and malaria programmes in rural Mozambique to running initiatives for people returning home after incarceration in New York City. Her leadership blends humility, deep empathy, and strategic thinking in some of the world’s most complex and under-resourced environments. You'll hear us discuss: Why waiting for full clarity before communicating is a luxury leaders can’t afford in crisis—and how honest, imperfect communication builds more trust than silence.How the sudden dismantling of USAID funding has devastated public health systems globally, and why leaders like Rebecca are having to reimagine their strategies on the ground with little information and no time.The importance of recognising how power—whether in a community, a boardroom, or a rural health clinic—operates subtly, and how sharing it must be an intentional, ongoing process.What it means to lead with purpose when your work is directly tied to life and death, and how personal connection—not metrics or strategies—often becomes the true driver of lasting impact.How Rebecca’s years in remote Mozambique taught her not only how to mobilise local expertise but also how to navigate and build trust in completely different systems, including the private equity world in Manhattan.Why the best social impact work isn’t born out of obligation or abstract logic, but out of deep personal passion—and how to find your own way into the work that truly matters to you. Resources Rebecca Vander Meulen on LinkedIn | J.C.Flowers Foundation Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    41 min
  8. Leadership Beyond Profit

    MAY 14

    Leadership Beyond Profit

    "The need for leaders who fund, champion, and drive social causes has only intensified — we need them now more than ever." - Winnie da Silva What if the most powerful leadership lessons aren’t coming from boardrooms—but from leaders fighting for dignity, justice, and community impact? In this episode of Transformative Leadership Conversations, I explore stepping beyond the walls of traditional leadership and into the world where return isn’t measured in revenue, but in real human impact. As someone who started my career in social work, this theme is personal. And now, with global funding shifts and social issues intensifying, learning from those who lead with purpose at the core feels more urgent than ever. You’ll hear me reflect on the values, challenges, and mindset of social impact leadership and how these insights can shape leadership at any level—whether you're scaling a non-profit, launching a start-up, or leading a legacy business. You’ll hear me discuss: The urgency of now: Why 2025 may be the hardest—and most vital—year yet for leading social change.Purpose over profit: What business leaders can gain from those who lead with mission at the centre.Leadership mindset shifts: Seven powerful lessons from the non-profit world that apply across every sector.Fundraising reframed: How telling your story and aligning others with your mission can fuel—not distract from—your work.Small scale, big impact: How one relationship-based programme quietly sparked new movements across the U.S.Innovation under constraint: Why limited resources often unlock the most creative, adaptive solutions.Leading through uncertainty: The importance of communicating—even when you don’t have all the answers—and staying grounded in your values.Upcoming guests: A preview of insights from Rebecca Vander Meulen and James Misner, two leaders who embody resilience and purpose in action. Resources Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org

    12 min

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Listen in on transformative conversations where leaders share their journeys as they overcome and thrive through adversity and change.

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